2-(phenylsulfonyl)benzaldehyde → HCID 59350822, compound

HRID 1644701Notes

Reaction equation

HRID 1644701 reaction equation
[BH4-].[Na+].[C:3]1([S:9]([C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH:14]=[O:15])(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[C:3]1([S:9]([C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14][OH:15])(=[O:11])=[O:10])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6409162-(phenylsulfonyl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 59350822HCID 59350822, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (690 mg, 18.2 mmol) was added to a solution of 2-(benzenesulfonyl)-benzaldehyde (1.98 g, 8.04 mmol) and methanol (50 mL). The reaction mixture was stirred at room temperature. When vigorous bubbling subsided, the reaction mixture was cooled in an ice-water bath, then carefully quenched with a 1.0 N aqueous solution of HCl (20 mL). The mixture was concentrated to remove methanol, then the residue was diluted with water and extracted three times with ethyl acetate. The combined organic phases were dried over MgSO4, filtered, and concentrated to afford 1.94 g (97%) of (2-benzenesulfonyl-phenyl)-methanol as an oil. This product was used in subsequent steps without further purification.

Workup

  1. customWhen vigorous bubbling
  2. temperaturethe reaction mixture was cooled in an ice-water bath
  3. customcarefully quenched with a 1.0 N aqueous solution of HCl (20 mL)
  4. concentrationThe mixture was concentrated
  5. customto remove methanol
  6. additionthe residue was diluted with water
  7. extractionextracted three times with ethyl acetate
  8. dry with materialThe combined organic phases were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-136e7dbaf7f648a4976879b2dabb8d7f
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

Loading…